The transfer of nitrene is a fundamental C—N bond formation reaction. It is well-known that many metal complexes function as a catalyst for the nitrene transfer reaction through a metal nitrenoid intermediate, and much efforts have been directed to an asymmetric nitrene transition reaction, especially aziridination and amination. Chiral metal complexes such as metalloporphyrins, metallosalens, Cu-bis(oxazoline), Cu-bis(Schiff base), Cu-diamine complexes and the like have been examined as a catalyst for the asymmetric nitrene transition reaction, and reported to have a high enantio-selectivity.
In the above reports, however, N-arylsulfonyliminophenyl iodinane (PhI═NSO2Ar) has been used as a nitrene precursor. In this case, there are problems that iodobenzene is yielded as a by-product and it is difficult to remove an arylsulfonyl group from a product.
On the other hand, there is reported an asymmetric nitrene transfer reaction using N-arylsulfonyl azide instead of N-arylsulfonyliminophenyl iodinane, but the enantio-selectivity in this reaction is insufficient or the severe reaction condition such as UV-irradiation, heating or the like is required for promoting the nitrene transfer reaction.
On the contrary, the inventors have reported that it is possible to conduct an asymmetric sulfimidation of an alkyl aryl sulfide and asymmetric aziridination and amination of an olefin with N-arylsulfonyl azide as a nitrene precursor at room temperature in the presence of a Ru(salen)(CO) complex without photo-irradiation (see Literature 1: M. Murakami, T. Uchida, T. Katsuki, Tetrahedron Lett., 2001, 42, 7071-7074, Literature 2: M. Murakami, T. Uchida, B. Saito, T. Katsuki, Chirality, 2003, 15, 116-123, and Literature 3: K. Omura, M. Murakami, T. Uchida, R. Irie, T. Katsuki, Chem. Lett., 2003, 32, 354-355).